[(2R,3S,4S,5R,6R)-6-[[(1S,12R,13R,17R,19S,20R)-9,20-dihydroxy-12-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-8,10-dimethoxy-3,14-dioxo-2,15,18-trioxatetracyclo[15.2.1.04,13.06,11]icosa-4,6,8,10-tetraen-19-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate

Details

• Internal ID: 8177f98b-04fa-4536-a3f7-945e668031ca
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: [(2R,3S,4S,5R,6R)-6-[[(1S,12R,13R,17R,19S,20R)-9,20-dihydroxy-12-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-8,10-dimethoxy-3,14-dioxo-2,15,18-trioxatetracyclo[15.2.1.04,13.06,11]icosa-4,6,8,10-tetraen-19-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC(=O)OCC1C(C(C(C(O1)OC2(C3C(C(O2)COC(=O)C4C(C5=C(C(=C(C=C5C=C4C(=O)O3)OC)O)OC)C6=CC(=C(C=C6)O)OC)O)CO)O)O)O
• SMILES (Isomeric): CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@@H]3[C@@H]([C@H](O2)COC(=O)[C@@H]4[C@@H](C5=C(C(=C(C=C5C=C4C(=O)O3)OC)O)OC)C6=CC(=C(C=C6)O)OC)O)CO)O)O)O
• InChI: InChI=1S/C35H40O19/c1-13(37)49-10-20-25(39)28(42)29(43)34(51-20)54-35(12-36)31-27(41)21(53-35)11-50-33(45)24-16(32(44)52-31)7-15-9-19(47-3)26(40)30(48-4)23(15)22(24)14-5-6-17(38)18(8-14)46-2/h5-9,20-22,24-25,27-29,31,34,36,38-43H,10-12H2,1-4H3/t20-,21-,22-,24+,25-,27-,28+,29-,31+,34-,35+/m1/s1
• InChI Key: DNNFVVSYJQJEAO-LCCFSMFLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₀O₁₉
• Molecular Weight: 764.70 g/mol
• Exact Mass: 764.21637904 g/mol
• Topological Polar Surface Area (TPSA): 276.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -1.43
• H-Bond Acceptor: 19
• H-Bond Donor: 7
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8050	80.50%
Caco-2	-	0.8820	88.20%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7365	73.65%
OATP2B1 inhibitior	-	0.7105	71.05%
OATP1B1 inhibitior	+	0.8254	82.54%
OATP1B3 inhibitior	+	0.9378	93.78%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9238	92.38%
P-glycoprotein inhibitior	+	0.6933	69.33%
P-glycoprotein substrate	+	0.6051	60.51%
CYP3A4 substrate	+	0.7103	71.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8786	87.86%
CYP3A4 inhibition	-	0.8885	88.85%
CYP2C9 inhibition	-	0.7832	78.32%
CYP2C19 inhibition	-	0.7695	76.95%
CYP2D6 inhibition	-	0.9229	92.29%
CYP1A2 inhibition	-	0.8417	84.17%
CYP2C8 inhibition	+	0.7192	71.92%
CYP inhibitory promiscuity	-	0.6977	69.77%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6371	63.71%
Eye corrosion	-	0.9869	98.69%
Eye irritation	-	0.9168	91.68%
Skin irritation	-	0.7813	78.13%
Skin corrosion	-	0.9407	94.07%
Ames mutagenesis	+	0.5146	51.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.7178	71.78%
Micronuclear	+	0.5374	53.74%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.8426	84.26%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.9389	93.89%
Acute Oral Toxicity (c)	I	0.3947	39.47%
Estrogen receptor binding	+	0.8747	87.47%
Androgen receptor binding	+	0.7007	70.07%
Thyroid receptor binding	+	0.5564	55.64%
Glucocorticoid receptor binding	+	0.7652	76.52%
Aromatase binding	+	0.6461	64.61%
PPAR gamma	+	0.7749	77.49%
Honey bee toxicity	-	0.6892	68.92%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9847	98.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.92%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.90%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.19%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	98.42%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.10%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.63%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.51%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.95%	86.33%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.82%	96.61%
CHEMBL2535	P11166	Glucose transporter	91.64%	98.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.31%	92.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.11%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.79%	95.89%
CHEMBL4040	P28482	MAP kinase ERK2	89.24%	83.82%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.82%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	88.66%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.37%	96.00%
CHEMBL2581	P07339	Cathepsin D	87.73%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.47%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.72%	99.17%
CHEMBL340	P08684	Cytochrome P450 3A4	85.22%	91.19%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.72%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.53%	89.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.25%	99.23%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.89%	97.21%

Plants that contains it

• Trigonotis peduncularis

Cross-Links

• PubChem: 102395472
• LOTUS: LTS0166275
• wikiData: Q104985647